Water → N-[2-[[6-[(3S)-3-methylmorpholin-4-yl]-2-[4-[(1-methylpyrazol-4-yl)methylcarbamoylamino]phenyl]pyrimidin-4-yl]methylsulfonyl]ethyl]acetamide

HRID 2353710

Reaction equation

HRID 2353710 reaction equation
ClC1C=CC=C(C(OO)=O)C=1.[OH2:12].[Mn]([O-])(=O)(=O)=O.[Na+].[CH3:19][C@H:20]1[CH2:25][O:24][CH2:23][CH2:22][N:21]1[C:26]1[N:31]=[C:30]([C:32]2[CH:37]=[CH:36][C:35]([NH:38][C:39](=[O:48])[NH:40][CH2:41][C:42]3[CH:43]=[N:44][N:45]([CH3:47])[CH:46]=3)=[CH:34][CH:33]=2)[N:29]=[C:28]([CH2:49][S:50][CH2:51][CH2:52][NH:53][C:54](=[O:56])[CH3:55])[CH:27]=1.[OH2:57]>O1CCOCC1>[CH3:19][C@H:20]1[CH2:25][O:24][CH2:23][CH2:22][N:21]1[C:26]1[N:31]=[C:30]([C:32]2[CH:37]=[CH:36][C:35]([NH:38][C:39](=[O:48])[NH:40][CH2:41][C:42]3[CH:43]=[N:44][N:45]([CH3:47])[CH:46]=3)=[CH:34][CH:33]=2)[N:29]=[C:28]([CH2:49][S:50]([CH2:51][CH2:52][NH:53][C:54](=[O:56])[CH3:55])(=[O:57])=[O:12])[CH:27]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 70297m-Chloroperbenzoic acidHCID 516876Sodium permanganate monohydrateHCID 59380043N-[2-[[6-[(3S)-3-methylmorpholin-4-yl]-2-[4-[(1-methylpyrazol-4-yl)methylcarbamoylamino]phenyl]pyrimidin-4-yl]methylsulfanyl]ethyl]acetamide

Product 1

HCID 59380059N-[2-[[6-[(3S)-3-methylmorpholin-4-yl]-2-[4-[(1-methylpyrazol-4-yl)methylcarbamoylamino]phenyl]pyrimidin-4-yl]methylsulfonyl]ethyl]acetamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

meta-Chloroperbenzoic acid (156 mg, 0.90 mmol) dissolved in Dioxane (2 mL), and sodium permanganate monohydrate (192 mg, 1.20 mmol) dissolved in water (1 mL) were added dropwise to N-[2-[[6-[(3S)-3-methylmorpholin-4-yl]-2-[4-[(1-methylpyrazol-4-yl)methylcarbamoylamino]phenyl]pyrimidin-4-yl]methylsulfanyl]ethyl]acetamide (162 mg, 0.30 mmol) in dioxane (6 mL) and water (2 mL) at RT under nitrogen. The resulting solution was stirred at RT for 1 hour. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M ammonia in methanol and pure fractions were evaporated to dryness. The crude product was purified by preparative HPLC using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents, to give the desired material as a white solid (61 mg).

Workup

  1. customThe crude product was purified by ion exchange chromatography
  2. washThe desired product was eluted from the column
  3. customwere evaporated to dryness
  4. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-7137156305b34f469a888bf9193aa96b
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Linked notes

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